The primary goal of the proposed research is to synthesize and study the chemistry of bifunctional alkylating agents of four major structural types. Three of the new systems under consideration are bis- aziridines, bis-oxiranes and bis-azirines of cyclophane dienes. The small strained rings will be introduced into the cyclophane dienes by established procedures from the literature. Also, through product studies and kinetic analysis we shall study the mechanisms of nucleophilic substitution of 2-arylsulfonyl allyl systems along with analogous reactions of model systems derived from 5-norbonem-2-ol. The synthesis of two types of bridged annulenes will be attempted and the chemistry of these substances as potential alkylating agents will be investigated. We shall attempt to correlate chemical and physical properties with carcinogenic and/or carcinolytic activity.